Potassium Carbonate → 1-Bromo-3-ethynylbenzene

Participants

Reaction Steps

To each of 2 one-liter flasks were charged K2CO3 (68 g, 493 mmol), a large magnetic stirbar and MeOH (250 mL). Stirring was begun on both reaction mixtures and once it was satisfied that they were stirring without any problems, 3-bromophenyltrimethylsilylacetylene (12.5 g, 49.3 mmol, 10.5 mL) was added to each reaction vessel and the mixtures were refluxed overnight. The reaction mixtures were filtered and the filter cakes were washed with MeOH. The combined filtrate was concentrated in vacuo, diluted with hexanes, and washed with water twice. The organic layer was concentrated to give a yellow oil. Flash chromatography (SiO2, Hexanes), provided 9.1 g, 50%, of the title compound as a colorless to light yellow oil. 1H NMR 500 MHz (CDCl3) δ 3.08 (s, 1H); 7.16 (t, 1H, J=7.89 Hz); 7.38 (dt, 1H, J=7.77 Hz, 2.44 Hz); 7.44-7.47 (m, 1H); 7.61 (t, 1H, J=1.68 Hz).

Provenance & Evidence